N-Hydroxyphthalimide → N-(3-methylisoxazol-5-yl)methoxyphthalimide

Participants

Reaction Steps

8.17 g of N-hydroxyphthalimide and 23.9 g of triphenylphosphine were added to a solution of 5.15 g of 5-hydroxymethyl-3-methylisoxazole in 245 ml of tetrahydrofuran. A solution of 13.3 g of dimethyl azodicarboxylate in 20 ml of tetrahydrofuran was then added dropwise at room temperature under an atmosphere of nitrogen to the resulting solution. The mixture was then allowed to stand for 30 minutes, after which the solvent was removed by distillation under reduced pressure. The resulting residue was purified by flash column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to afford 7.21 g of N-(3-methylisoxazol-5-yl)methoxyphthalimide, melting at 129°-131° C.

Provenance & Evidence